Desperate Times Call For Desperate Measures
by fangirl1011
Summary: A year ago, Skylar Monroe stayed with Sam and Dean Winchester, but she left to find the reason she started hunting: her father. Now she has a lead and the Winchesters show up. Dean is the only one who knows her secret. He's determined to help her, but she knows what will happen if he does. When she finally comes face to face with her enemy, she may just wish she had let Dean help.
1. Chapter 1

"Agent Mulligan, FBI." I showed the officer my badge.

"Over there." He pointed to the backyard, but I went inside to talk to the family first.

"Hi, Mrs Bradshaw? I'm Agent Mulligan with the FBI. Do you mind answering some questions for me?"

"Oh, uh, sure." I sat down next to her.

"First, I want to say I'm so sorry for your loss." She nodded.

"I don't understand why someone would do this to Terry. She was the sweetest person alive."

"I swear to you that I will do everything I can to find the person who did this to your sister. I won't stop until I find them." She started crying, and hugged me.

"Thank you," she sobbed, sitting up straight again.

"It would be my pleasure to get justice for your sister. But in order to do this, I need to ask you some questions." She nodded.

"Of course. Anything to help."

"Did your sister mention seeing anyone follow her or anyone who took an interest in her?"

"No, nothing. She was seeing someone, but he disappeared a couple weeks ago."

"What was his name?"

"Dennis Wilson." I made a note to look into his case file specifically. "He was a sweet guy, too. They were perfect for each other. I think he was going to propose to her, you know."

"How often did you talk to your sister?"

"Everyday. I knew something was wrong when she didn't pick up last night, but my husband said she probably fell asleep watching SVU reruns. Terry did that sometimes, but I had to come check when she didn't pick up this morning. I couldn't find her in here, so I went out back and found her like that." She started sobbing again, so I placed my hand on her back.

"Just one more question. When you came today, did you see anything out of place?"

"No."

"Okay. Thank you so much, Mrs Bradshaw. Here's my card. Call me if you need anything at all."

"Thank you." I smiled, and went out back to check the body.

"You the FBI lady?" a balding man asked. He was crouched next to the body, so I assumed he was the medical examiner.

"Yes. I'm Agent Mulligan."  
"Well, then, you might want to take a look at this." I crouched down to get a closer look. Two almost microscopic holes in two different places on her neck.

"Are those needle marks?"

"Yup. They punctured the jugular and the carotid." I sighed. "You seen this before?"

"A few times."

"And you never caught the guy?"

"He left no evidence. I'm gonna get this son of a bitch this time, though." I stood up, and walked away.

I knew exactly who did this. It was the same monster that killed my mother. But I knew what I was doing this time. I wasn't going to run. I was going to track down and kill my father. No way was I waiting for him to resurface in another five years.

"Skylar?" I turned around. "Hey."

"Hey, Sam. Dean." Sam smiled while Dean just nodded in my direction. A blonde chick got out of the Impala, and I thought maybe they really had moved on. But then I saw her face. "Is that-"

"Our mom, Mary Winchester. The Darkness brought her back."

"Wow." Mary smiled at me. "Hi."

"Hello. What's your name?"

"Skylar. It's nice to meet you."

"You, too. Are you friends with my boys?"

"Kind of. We worked together for a while." Sam shifted his weight.

"So Skylar, do you think this is a vampire?"

"Not unless vampires use needles now." He frowned. "Just a human psychopath, I'm sure."

"Oh." I accidentally met Dean's eyes. He was the only one who knew the real reason I was a hunter.

"Just a human?" he asked suspiciously.  
"Looks that way. You guys are welcome to check it out, of course, but I really don't think it's anything supernatural."

"We trust you." Dean was still staring at me. I was pretty sure he suspected it was my dad and that I was going to go after him on my own. "Why don't you come over for dinner tonight? Our mom's cooking."

"Actually, I have another hunt to work on."

"You can't stop for a couple hours?" He gave me the puppy eyes.

"I suppose I can take a break."

"Sweet!"

"Hop in," Dean said. "We can ride back together."

"Alright." I got in the back, but then I noticed Dean hand Mary the keys.

"I'll take the back for the ride home." She shrugged, and he slid in next to me. He had sent me a text before the car was even started.

 _Is this the work of your dad?_

 _Does it matter?_

 _Yes._

 _Why?  
Because you get reckless when you think it's your dad._

 _Thanks for your concern, but I'll be fine. You know I didn't tell you the truth so you could stop me from hunting him._

 _I would've banned you from hunting vamps all together. You get reckless._

 _I can take care of myself, Dean._

 _Really? What about last time?_

I glared at him, and stuffed my phone into my blazer pocket. I didn't need any reminders from him what happened the last time I had a lead on my father. The only difference was I was going to finish the job this time.


	2. Chapter 2

"That was amazing, Mary," I said. We'd had chicken, mashed potatoes, corn, and biscuits. Like, a real chicken, too. "Thank you guys for having me over."

"I'm so glad you liked it!" I really liked the boys' mom. She was so nice.

"Do you need any help cleaning up?"

"Sam can help me. You're our guest. You shouldn't help clear the table." She took the dishes into the kitchen with Sam, leaving Dean and I alone.

"Need any help on your case?" he asked.

"You just won't let it go, will you?"

"What if he's luring you in and you get turned trying to kill him?"

"Then, we'd be on an even playing field. This is _my_ case and _my_ responsibility. I didn't kill him when I had the chance, and look what happened. An innocent woman is dead. I can't change the fact that she's dead, but I can make sure nobody else dies. I won't make the same mistake again."

"First rule of hunting: you can't save everyone. Even if you had succeeded last time, that lady still could've died yesterday from anything. Don't get yourself killed because you feel guilty."

"I will do what it takes."

"And that includes dying?"

"You and Sam were ready to die taking out Azazel."

"That's different."

"Is it?" My phone chimed, saving me from Dean.

 _Cara: Another death. Only three hours old. Scottsville, Kansas._

"Skylar?"

"I have to go." I stood up.

"What happened?" Judging by the look on his face, he already knew.

"Are you leaving already?" Mary asked.

"I'm afraid I have to. My friend was… in a car accident. She's fine, but I really should go."

"Oh. Alright. Be safe."

"Thanks for tonight. It was probably the best dinner I've had in a year and a half."

"It was my pleasure. Don't be a stranger."

"I won't."

"I can drive you back," Dean volunteered. "It would be faster than a bus."

"I don't want to trouble you." I tried to warn him to back off, but maybe that only encouraged him.

"No trouble at all." And that's how I ended up in the Impala with Dean.

"You really like to push my buttons, don't you?" I asked after a while.

"You should know that by now. Besides, maybe I can help at this crime scene."

"If I have any say, and I do, you're not going anywhere near my crime scene."

"Your crime scene? You're not a real FBI agent."

"No, but I can act it. When it comes to asking questions, subtlety is the one thing you and Sam don't have."

"We can be subtle."

"I haven't seen any signs of subtlety from you. You just ask for any weird smells or where the deceased is buried. Which, by the way, you can look up."

"Well…" I smiled. "Shut up." I looked out the window at the trees blurring past.

"Your mom is nice. I like her."

"Yeah, she's awesome." He smiled. I liked seeing Dean smile. "Anyway, we're almost to Scottsville. Another fifteen, twenty minutes, maybe."

"Good. I want to get on his trail before it goes cold."

"I bet."

"What is that supposed to mean?"

"Just that you're… motivated."

"Of course I am. He's killing people because I let him get away. And don't you dare tell me that it's not my fault."

"It's not."

"Dean."

"Alright, alright." Don't get me wrong, I appreciated his concern, but I didn't need a reason to back out, not now that I was close. "Just one more question."

"What?"

"Why didn't you say goodbye in person?"

"It wasn't as hard and you couldn't talk me out of it."

"So you just left the note and hoped we wouldn't try to find you?"

"Yeah. Although, part of me wished you would find me."

"Why?" I stared at him.

"It doesn't matter now. Things have changed and I have a job to do." He turned onto the street with police cars on it. "Thanks for the ride."

"Yeah, sure." He pulled to the side, and I climbed out. "Hey, Skylar?"

"Yeah?"

"You know where to find me if you need anything."

"Yes, I do. Bye, Dean."

"Bye." I ducked under the police tape, showed them my badge, and then continued into the house.

"I didn't think you'd be this long," Cara said. Her long brown hair was pulled into a ponytail and her matching eyes had dark circles under them. She wasn't a hunter, but a real FBI agent. I helped her out a while back, so she helped me find cases sometimes. I had asked her to keep a look out for these types of cases for me.

"Traffic. Where's the victim?"

"Kitchen, but brace yourself." Curious and slightly scared, I went into the kitchen.

As soon as I saw the body, I knew what he was doing. He was luring me in by killing people like his first victims. This one was a little girl, no more than six. She had jet black hair and her lifeless blue eyes were open and staring at me. I fought down the urge to vomit.

"That son of a bitch," I whispered.

"I warned you," Cara said, sounding sick herself. "So? Can you, uh, predict where he's going next?"

"I don't think he's going anywhere."

"Why?"

"You read the file. Who does this little girl look like?" She looked at the girl, and her mouth formed a silent 'oh.' "Yeah. I'm his end game. He's waiting for me."

"Are you going to find him on your own?"

"Yes. And I am going to take him out." I turned around, and walked out.


	3. Chapter 3

I did throw up once I got outside. I couldn't believe he had ended that little girl's life like that. Actually, I could, but it didn't make me feel any better. In fact, it made me feel worse.

"Hey." I looked up. Dean was standing next to me.

"I thought you left." I brushed off his concern, wiping my mouth with my sleeve.

"I did, but then I saw a diner with amazing looking pie. Then, I realized forgot my wallet." I gave him my best 'Really?' look. "You okay?"

"Never better."

"Really? Because you don't look okay."

"I'm fine, Dean."

"Now I know how Sam feels," he mumbled.

"What was that?" I snapped.

"Nothing." I glare at him, but then something catches my eye over his shoulder. A familiar face, one I hadn't seen in decades. He smirked, and then disappeared in the blink of an eye. "Skylar?"

"Hmm?"

"What is it?" He turned around, trying to figure out what I was staring at.

"I just thought I saw an owl. You know how much I like owls."

"Right." He eyed me suspiciously.

"You wanted pie, right? Well, let's go. I'm buying."

"Okay?" I walked quickly over to his car.

"Can I drive?"

"Over my dead body." I shrugged.

"Worth a shot."

The pie really was great, but not as good as the company. We kept it lighthearted, so nothing hunting related. I mostly listened while he talked about Sam and Mary. I was surprised when he said Cas was addicted to Netflix. Last time I saw him, he couldn't even work a remote.

"You're kidding?"

"Nope. He's been watching _Game of Thrones_ recently."

"I don't believe it."

"It's true." Setting the check on the table, the waitress winked at Dean. I rolled my eyes, but then kicked his leg when he started checking out her ass. "Ow!"

"Stop it."

"Sorry, geez. You're worse than Sam."

"I'm taking that as a compliment." I left the money on the table.

"Thanks for the pie," he said as we walked out to his car.

"My pleasure."

"You want me to take you anywhere?"

"No, I'm good. There's a motel not far where I'll spend the night, and I'll pick it up again tomorrow."

"Skylar, don't get me wrong. I'm glad we had the chance to have a normal conversation over some of the most delicious pie ever," I chuckled, "but you had to have known that wasn't going to last long." I sighed.

"Yeah, I know."

"So what's bugging you?" The image of that little girl popped into my head, which brought an image of my sister along with it.

"It's just that the bodies are beginning to pile up. It's not like last time."

"It's not too late to invite us in."

"No!" He seemed surprised at my outburst.

"I'm just trying to help."

"Yeah, well, I don't want your help!" I didn't know why I was still shouting. "Just go home, Dean. I can do this on my own."

"Just-"

"Dean, go."

"Fine." He got in his car, and drove away.

Dean's Impala had just disappeared from view, when something hard hit the back of my head. I crumpled to the ground.

"Finally." The voice sounded somewhat far away, but I recognized it. I tried to push myself up, but my assailant put his foot on my back.

"You bastard." He ignored me.

"You know, I considered hurting your boyfriend, too, but I just want you, angel."

"Fuck you."

"That's no way to talk to your father, Skylar."

"My father died twenty seven years ago." He growled. I was trying to stay conscious.

"I believe you're mistaking me with your mother and Emma." At the sound of Emma's name, a rush of energy flooded my veins. I mustered up enough strength to roll over, knocking my father over in the process. I went to grab the blade I kept in my pocket, but it wasn't there.

"What the-"

"Looking for this?" I looked up to see my father holding my blade. "I'm surprised at you, Skylar. After last time, I thought we agreed that you can't even try to kill me."

"Things have changed."

"I haven't." He was right about that. He still had his salt and pepper hair and tan skin. "Oh, you meant my victims. Yeah, little Sarah had no idea what was about to happen to her. She was just coloring a picture for her mommy." I growled.

"You sick son of a bitch."

"I've had enough of your attitude, young lady. I think it's time for bed." Again, I was hit from behind, but with much more force. I was out in a few seconds.


	4. Chapter 4

The smell of blood was the first thing my brain recognized when I woke up. I had no idea what time it was, but I assumed it was hours later than it had been when I was knocked out. My head hurt to the point where I actually wanted to die just to get rid of the pain. I had a feeling I was about to get a lot worse, though.

The room was dark, but I got a little amount of sunlight. Based on the amount, I had a feeling it was about sunrise. I looked around and found out why I smelled blood. It wasn't mine, clearly, or I'd be dead. There were bags in a fridge and a bucket in the corner. His supply, I realized. This was why it was taking so long to find him.

"Where are you, you son of a bitch?!" I called out. The sound of my own voice felt like an ice pick to me.

"How many times do I have to tell you to watch your mouth?" Slowly, my dad stepped into the light. "It's not lady-like to swear."

"Well, I've never been lady-like."

"True. You always were your mother's little rebel." I clenched my teeth. "Unless you were around Emma. Then, you were like a whole other person."

"Don't you say her name," I growled. "You have no right."

"Don't I? She was my daughter, after all." I lunged, but only ended up hurting myself. I almost dislocated my shoulders. "Now, now, Skylar. We don't want you getting hurt." He stepped closer, but then hissed and jumped back. He had stepped into a patch of sunlight.

"You just made my week," I said, smirking. He glared at me.

"Lucky for you, you have until the sun sets to imagine the fun we'll have later." He snapped his fingers, and a boy, no more than sixteen, appeared at his side. "You know what to do."

"Yes, sir." My dad left, leaving the boy with me.

"What's your name?" He looked at me.

"Luke."

"Have you… you know?"

"Killed someone? No. I'm not even a vampire yet. I'm just here for show, mostly."

"You're not a vampire?" He shook his head. "Then, why the hell don't you leave?"

"He has my sister a little way away. I promised to do whatever he wanted me to do as long as he doesn't kill her. I get to see her every couple of days. She's well taken care of, though, so I can't really complain."

"You'll know you'll both be meals one day, right?"

"I'm a hopeful person."

"Lucky you," I muttered.

"You want a drink?" He walked over to a fridge I hadn't noticed before, and pulled out a water bottle.

"I'll pass."

"You really should drink something."

"Not thirsty."

"Oh. Alright, then. Just let me know when you need one." A few minutes passed in silence.

"Do you have a phone?"

"No."

"What if I said that if you helped me, I could help you?" He looked over at me. "You must know where your sister is."

"So? I'm not going against a vampire, especially not one like Jack."

"I could buy you tons of time to get your sister and get someplace far away from here." He looked like he really wanted that, but then shook his head.

"Even if you could, you'd be killed and he has our scent."

"Have you ever heard of hunters?" Luke shook his head. "Well, I'm a hunter. We hunt monsters like Jack. I can kill him, but first I need your help." He stopped what he was doing.

"What sort of help would you need?"

"A blade of some sort." He pulled out a knife that looked eerily similar to mine.

"He gave it to me when he got home last night." So it was mine. "He said to use it only if you somehow escaped."

"Good. Then, I'll need you to untie me."

"I don't think I can help you."

"Just hear me out." He nodded. "You sneak out that open window. He can't chase you in daylight. You run, get your sister, and go to California or Florida, someplace where it's almost always sunny. I'll take care of him, and you and your sister can go live a long, healthy life." He looked at the window. "You have to know how much sunlight hurts him. Plus, he really only wants me. I doubt he'll even think about you once he sees I'm free."

"No," he said, but gave me a smile. "I'm not stupid." This kid was way smarter than I originally thought. He walked over and cut the ropes holding me in place. He quickly handed me the knife, and pushed open the window.

"Run and don't look back," I whispered. He nodded, and climbed out.

"You were right about one thing." I froze. Not part of the plan. "I'm really only concerned with you."

"I thought vampires slept during the day."

"Usually, but I heard you trying to bribe Luke. I knew he'd take it."

"He's smart."

"Yes, he is, which is why I kept him around. It's a shame he's gone, but I still have what I want."

"Then, come get me." I smirked, knowing he wouldn't. I was standing in a patch of sunlight.

"The sun will set eventually." He was right, but I had a weapon. Not a great weapon, but it was better than nothing.

I hoped.

"Do you remember when we use to go on picnics in that park near our house. You were just obsessed with the swings. Your mom used to push you higher and higher. You thought you could touch the sky if you went high enough."

"Every kid thinks that."

"True. Except Emma."

"Are you trying to piss me off?"

"She was such a sweet girl." My knuckles turned white. "She tasted even sweeter. Like chocolate. No, strawberries." I lunged.


	5. Chapter 5

I was an idiot. I played right into his plan to lure me out of the sunlight. He knew exactly what to say to piss me off, too. I lunged, and managed to stab him except he moved at the last moment. The knife plunged into the upper part of his shoulder. Where else would it go? This was happening to me, remember.

"Always acting before you think," he growled, pulling the knife from his shoulder. He tossed it into the bucket of blood. I tried to make it back to my little patch of sun, but he was faster. "You should've listened to Dean, angel."

"Casti-" He put his hand over my mouth.

"No calling the angel, angel. It's time to join your sister." In a panic, I bit him. "You bitch!" He let me go, and I ran away from him. I didn't go to the sunlight, though. I knew that it wasn't safe for me anymore. Surprisingly, Jack started to laugh.

"Why are you laughing?"

"This is way better than my original plan. There's vampire blood in you now." I touched my mouth to see that I did get his blood in my mouth. I didn't think I'd broken skin. "And that is a much worse fate than dying. I wonder if it will be Dean who kills you."

I didn't trust myself to feel around in the bucket of blood, so I ran around my father, hoping to find something sharp in the other room. I had to wait for my eyes to adjust before I could look around. There was a living room area, a knight's armor in the corner, and a sword high up on the wall. I was about to run for it when something grabbed hold of my wrist.

"Where do you think you're going?" I grabbed onto Jack's arm with my free hand, and twisted it as far as I could until he let go. Then, I shoved him as hard as I could. He stumbled, falling into his bucket of blood.

I didn't waste my time. I pushed the couch up against the wall, but I didn't quite make it. I was pulled away and thrown back into the wall on the opposite side of the room. I surprised myself when I growled at Jack.

"You're irritating me, angel," he said. His lips and chin were dripping red. He obviously just fed.

"Yeah? Well, you've been irritating me for the past eight years." I kicked him in the jaw, and ran towards the couch. My fingers were only an inch away when I was pulled away again.

"I've had enough of this." His teeth sank into my neck, and I could feel my body weakening.

Images of Emma and my mom played like a movie before my eyes. I saw myself escape and run while she died at the hands of our father. Then, there was flirting with Dean in that bar and being so drunk I spilled my guts about that night and how I was hunting him. I saw our moments in the bunker and then teaching Cas how to cook. I studied lore with Sam while Dean and Cas hunted, snuck into Dean's room when my nightmares became unbearable. I saw myself writing the note and leaving and then seeing them almost two years later. Dinner with Mary and the boys and then pie later on with Dean, my friend Cara and her concern for me, and finally watching Luke run.

Hit with a sudden surge of strength and motivation, I elbowed Jack in the ribs. He hissed, releasing me. I knocked over the coffee table and the knight on my way to the couch, hoping they would give me enough time to get the sword. Finally, my fingers wrapped around the hilt of the blade.

"Think about what you're about to do," Jack said. I guess he was trying to save his life by begging. Honestly, I wanted to see him beg, just like my sister begged.

"I have. I've thought about it for years." I jumped down off the couch.

"I have enough blood to last us a year. We could be a family again, angel."

"And why would I agree to this?"

"I was a new vampire then. I didn't know what else to do."

"You were always a sadist. Being turned just gave you an excuse to torture us."

"Now, angel, I-"

"Shut up." I pressed the side of the blade to his throat. "You tortured us for days. Emma was still only a child. And when she cried, begged you to stop, you laughed and walked away. Finally, when the waiting and torturing got boring for you, you killed her, drained her. Do you remember what she did in her last moments?" He swallowed hard, and shook his head. "She told me to run. You killed someone so… good." I pulled the sword back. "You're a monster, and I am going to kill you once and for all." I swung with all my strength.

I collapsed onto the couch. Despite what Sam and Dean had told me, I really thought revenge would make me feel better. And though a weight was lifted, there was still something missing in my soul. After a few minutes of savoring my victory, I remembered that I was a monster now, too.

"Cas," I said, my voice weak. "Cas, I need your help. Please." A split second later, Cas was standing in front of me.

"What happened?" he asked, looking around.

"I need a favor." He stared at me. "I need you to kill me."

"Why?"

"I didn't have a choice. I swallowed vampire blood."

"Skylar-"

"Cas," I stood up, and walked over to him, "please. I don't want to hurt anyone. Kill me now while I'm still somewhat human."

"There are alternatives."

"I've done what I needed to." He looked… sad. "I want this, Cas. Just do it."

"Okay."

"Tell the boys I said goodbye." He placed his hand on my head.

"I will." I waited for him to kill me, but nothing happened.

"Cas?"

"I can't do it." I groaned. "Not when there are alternatives."

"I'm not going to argue with you."

"You're not?"

"No. I think I've fought enough." Holding my breath, I walked over to the tipped over bucket, and picked up the knife. "Goodbye, Cas." I brought the knife to my neck, and then everything went dark.


	6. Chapter 6

I woke up. I was confused to say the least. I thought I had died. I suppose, however, I should've realized I wasn't dead when I didn't end up in Purgatory. This place was new, though. I tried to move my hands, but they were strapped to the chair I was in.

"Skylar?" I looked up.

"Dean?" He stood by a table in the corner of the room. "Where am I?"  
"The bunker. This is our dungeon." The Men of Letters were strange. "Cas told us what he could. How could you try to kill yourself?"

"How could I not? I'm a… vampire."

"Cas said he told you there were alternatives."

"And I didn't want to hear them. I won't risk taking somebody's life because I didn't die when I should've. Besides, the only reason you're offering me these alternatives is because you know me. It's the only reason Cas didn't kill me when I asked him to." He walked over, and undid the wrist straps. "Dean, stop!" He stepped back.

"If you're just like every other vampire we hunt, prove it."

"Are you serious? I could kill you."

"Yeah, but you won't even try."

"You don't know that!"

"You're not a monster. You never were." His faith in me was touching, but I wasn't as sure of myself as he was.

"Dean?" Sam walked in. "Look who's awake. How are you feeling?"

"Seriously? How can you two be so confident in me?" He looked at Dean.

"You didn't tell her?"

"I was getting there."

"Skylar, you're not a vampire," Sam said.

"What?" He pulled out his phone, hit a button, and then handed it to me. I checked my gums in his camera. "How is that possible?"

"There's a cure." I glared at Dean.

"So you just let me think I was going to kill you?"

"I was proving a point."

"The point is," Sam interrupted, "you're fine. Cas made lunch. Come on."

"We'll catch up," Dean said. Sam shrugged and left. "Uh, how are you feeling?"

"I'm fine."

"Talk to me." He stared at me with those emerald eyes.

"I feel better knowing he's dead and that I'm the one who did it. I'm not a hundred percent, but what hunter is? Now come on. We should go eat." I walked away.

Lunch was… good. And I'm not just talking about the food. Nobody brought up my hunt gone bad and it was a lighthearted conversation just like dinner had been. Afterwards, I helped Cas clean up.

"We need some stuff," Dean said as we finished doing the dishes, "so I'm gonna make a supply run. Skylar, you wanna come with?"

"Uh, sure." I set the dishtowel down, and followed him out to the Impala. "Why didn't you take Sam or Cas like you usually do?"

"Because I want to take you. Is that a crime?"

"No, just odd."

"Well, it's been an odd couple of days." I sensed ulterior motives, but got in the car.

Let's just end this story with an almost two day long supply run.


End file.
